K. Oguni et al., C-13 NUCLEAR SPIN-SPIN RELAXATION-TIMES (T(2C)S) OF ENANTIOMERS IN THE PRESENCE OF COLUMN PACKING MATERIAL AND SOLVENTS FOR CHIRAL DISCRIMINATION HPLC, Chirality, 8(5), 1996, pp. 372-376
To elucidate chiral recognition difference between pairs of enantiomer
s which interacted with a cellulosic stationary phase of chiral discri
mination high performance liquid chromatography (HPLC), C-13 NMR spect
roscopy was applied for enantiomers of 1-phenylethanol, 1-indanol, 1,2
,3,4,-tetrahydro-1-naphthol, glutethimide, and Troger's base. Their C-
13 nuclear spin-spin relaxation times (T(2C)s) and spectra were obtain
ed in deuterated HPLC solvents in the presence of column packing mater
ial made of cellulose tris (4-methylbenzoate) coated on silica gel. Th
e first-eluted enantiomers on the HPLC showed longer T(2C)s and strong
er signal intensities of C-13 NMR spectra than the second-eluted enant
iomers. These results indicated that the chiral recognition difference
of enantiomers was observed by their T(2C)s and intensities of C-13 N
MR spectra. The T-2C difference was found to reflect the retention ord
er of enantiomers on the chiral HPLC column. (C) 1996 Wiley-Liss, Inc.